President Barack Obama is rolling the dice again: he’s desperate to avoid getting dragged into a war over Iran’s nuclear program and appears to have restrained Israel — at least for now — from starting one by promising he’d do it himself if Tehran tried to build a nuclear weapon. And that means he really needs to make a success of the renewed diplomatic process he and Western allies are about to undertake with Iran. That reason alone should place by the President’s bedside Trita Parsi’s A Single Roll of the Dice: Obama’s Diplomacy with Iran, even if its critique would make uncomfortable reading for a President who may genuinely believe he has tried serious diplomacy with Iran. Based on interviews with dozens of top decisionmakers in the U.S., Iran, Israel and other stakeholder countries, Parsi concludes that the Obama Administration’s efforts were fatally flawed because of the domestic political limitations and time constraints imposed on diplomacy, and Iran’s domestic political turmoil. I asked Parsi, who is also the president of the National Iranian American Council, what five pointers he’d offer if asked by the White House for tips on improving the prospects for successful diplomacy with Iran. Herewith, Parsi’s answers:

Lesson 1: Don’t allow the domestic politics to define your strategy

The conflict between U.S. and the Islamic Republic of Iran is three decades old and has been created, perpetuated and reinforced at different points by the domestic political dynamics on both sides. Today, rather than negotiating with Iran itself, much of the Obama Administration’s Iran effort is actually negotiation with various power centers in Washington and abroad over how to deal with Iran. And that tends to anchor his strategy to the existing political landscape in ways that don’t bode well for diplomatic success. The Iranians face a similar problem.

As I point out on in the book, one of President Obama’s key mistakes was his failure to create political space for himself to engage with Iran. He didn’t use the political capital generated by his election to broaden his room for maneuver on Iran issues, because he didn’t want to make Iran a matter of domestic political debate in the way that we see it occurring now on the presidential campaign trail. But that meant that those negotiation efforts he did undertake were self limiting, in that the agenda was narrow — confined to the question of Iran’s willingness to accept Western and U.N. demands on its nuclear program — and that the time frame for such negotiations was deliberately limited, so as to avoid charges from more hawkish quarters that Iran was being allowed to play for time. Hence the “single roll of the dice” of my title, which was a phrase that an Administration official had used to define the limited negotiation efforts pursued by the Obama White House.

A single roll of the diplomatic dice with Iran is unlikely to work any more effectively this time than it did in 2009. The best-case outcome is going to require a process that will take time and will require a willingness on both sides to make concessions in search of a solution that both can live with. And in order to achieve that, President Obama is going to have to create the political space for himself at home that sustains that process.

The same problem exists on the Iranian side, of course, where the system’s fratricidal political conflicts have long bedeviled attempts at engagement with the West. All the more reason for a sustained process rather than a single roll of the dice. And we’re not going to get anywhere if we allow the crippling domestic political environment to drive the process.

Lesson 2: Broaden the agenda beyond the nuclear program

The decades-old enmity and tensions with Iran are hard enough in themselves; to confine diplomatic engagement with Iran to a single variable — the nuclear issue — which also happens to be the most intractable issue between the different sides right now, doesn’t enhance the prospects for success. In 2009, the Obama Administration effectively made confidence-building measures on the nuclear front the precondition for any wider conversation; until they were ready to do what we asked on that front, we refused to talk to them about anything else — even Afghanistan, on which the Bush Administration had actually engaged fairly productively with Tehran for a time, or on the issue of human rights.

There’s no way for the parties to avoid the nuclear question, of course, but that shouldn’t preclude discussion on other issues on which the sides can more easily find common ground and cooperate. The advantage of a broader agenda is that it potentially creates a dynamic of cooperation that can possibly help to create a measure of good faith that helps overcome obstacles and unblock the impasse to finding a solution to the nuclear question.

Lesson 3: Bring mediators into the conversation

The process the Administration is currently using for talks with Iran — negotiations between Iran and the P5+1 group [the U.S., Britain, France, Germany, Russia and China] is flawed, because there is no trust between the countries in the P5+1 and Iran. The Obama Administration has worked hard to make the P5+1 present a united front to Iran behind nuclear demands, and backed by limited U.N. sanctions. The reason for this strategy was to prevent Iran being able to play off different members of the P5+1 against one another. But bringing those countries closer to the U.S. position — albeit with major differences in their views on the nature of the nuclear issue in Iran, and how it may be resolved — has limited their ability to reach out to Tehran. So, these negotiations occur in an atmosphere of little trust. Prospects for progress will be greatly enhanced with help from countries that have relations of trust with both sides, such as Turkey and Brazil. The purpose of drawing them in would not be to replace the P5+1, but to complement its work by injecting more mutual confidence into the process. These are countries that don’t have the same domestic political restraints on their negotiation abilities as does the U.S. and some of the other Western countries. And President Obama knows from experience the role they can play in forging breakthroughs — in 2010, Brazil and Turkey managed to get Iran’s agreement to a fuel-swap deal, which was rejected by the U.S. as insufficient, even though Brazil and Turkey insist that it followed the terms laid down in a letter by Obama.

Lesson 4: Get real on uranium enrichment in Iran

The cat is out of the bag when it comes to the question of Iran enriching uranium for its nuclear program, thanks in no small part to the efforts of Prime Minister Benjamin Netanyahu to force President Obama to declare his red lines. The Bush Administration had drawn a red line at Iran “mastering the technology of enrichment” — but Iran crossed that line six years ago, and once a technology is mastered, it can’t be unlearned. Still, Israel, France and many in Washington had insisted that Iran could not be allowed to enrich uranium on its own soil, even in a certifiably peaceful nuclear program, because that technology gives Iran the means to build a bomb. The Obama Administration had been more ambiguous on the issue, at some points signaling a zero-enrichment policy and at other points accepting that once Iran had taken the steps necessary to assure the international community of its peaceful intent, it could exercise all the rights of a signatory of the Non-Proliferation Treaty — which would include enriching uranium.

Netanyahu insisted that Obama draw his red line, and the President did so — at weaponization of nuclear material by Iran. The zero-enrichment demand was untenable to begin with; now President Obama needs to convince the French, and the Israelis and others at home that the best deal that can be achieved with Iran is one that verifiably contains Iran’s nuclear program within verifiable limits that prevent weaponization. The advantage of pressing this goal now is that, as the Bush Administration learned, a solution that establishes confidence in Iran’s intent remains elusive the more the West clings to the demand for Iran to abandon all enrichment, while Iran continues to make progress that creates irreversible facts on the ground.

Lesson 5: Sanctions only work if they can be lifted

America’s leverage in the standoff with Iran depends not only on its ability to impose sanctions but also on its ability to lift them. The confidence-building concessions that the Western powers are going to demand of Iran — most immediately, it seems, the suspension of enrichment of uranium to 20% and the removal of Tehran’s stockpile of uranium enriched to that degree — can only realistically be achieved by offering Iran something that it needs. And Iran is very likely to demand steps toward lifting of sanctions, particularly those sanctions that most painfully affect Iran’s economy, i.e., those that impede its ability to sell oil and use the international banking system to trade on world markets. There have been reports that what the Western powers will offer in exchange for ending 20% enrichment will be a promise of no new U.N. sanctions against Iran, but that’s unlikely to impress Tehran: right now the U.S. is unable to win Russian and Chinese consent for new U.N. sanctions anyway, and those currently in force are of negligible effect on Iran’s economy. The sanctions that hurt Iran are those unilaterally adopted and enforced on others by the U.S. and the Europeans. And if some easing of those sanctions is not on the table from the U.S. side because an election-year domestic political environment militates against making concessions to Iran, then the U.S. will have to adjust its asks of Iran. Tehran is unlikely to be willing to give up something substantial in exchange for something it might deem insubstantial.

Moreover, by dramatically escalating sanctions — for example, cutting Iran off from the SWIFT system for processing international banking transactions last weekend — at the very same moment that a new round of talks has been scheduled reinforces an impression in Tehran that the U.S. goal is regime change, and that no concessions by Iran would be likely to stop the momentum of sanctions.

The Western powers go into the coming talks needing to hear that Iran is willing to offer complete transparency in its nuclear work, submit to the Additional Protocols of the Non-Proliferation Treaty that allow for more intrusive inspections and take verifiable steps that strengthen international confidence in the nonmilitary nature of its nuclear program. But for Iran to embark on a process, it needs to hear acceptance of its bottom line of retaining a civilian nuclear program, including the enrichment of uranium, if it submits to stricter procedures to verify its intent, and also that if Iran makes concessions, it will expect concessions from the other side.

And looking at Washington, right now you have to wonder whether President Obama can actually ease or lift sanctions, many of which — the SWIFT system cutoff would be the latest example — are acts of a far more hawkish Congress rather than Executive Orders by a President looking to use sanctions pressure to improve prospects for a deal. In Tehran’s view, Washington has a credibility when it comes to its carrots, not its sticks. The balance between pressure and engagement during the Obama presidency has been radically tilted in favor of pressure — diplomacy has been given all of three weeks, sanctions three years. Sanctions pressure, of course, may seem the politically least costly option, but it’s not necessarily the most effective one. To get a concession at the talks, and to get a process going, it is necessary to both demonstrate the willingness and ability to lift sanctions, granted that the Iranians accept significant limitations to their nuclear work.

Tony Karon is a senior editor at TIME, where he has covered international conflicts in the Middle East, Asia, and the Balkans since 1997. A native of South Africa, he now resides with his family in Brooklyn, New York.